Ring Transformation of 1,2‐Disubstituted 4(1H)‐Quinazolone Oximes to 3,5‐Disubstituted 1,2,4‐Oxadiazoles

Dezsó Korbonits, Ida Kanzel‐Szvoboda, Csaba Gönczi, Kálmán Simon, Pál Kolonits

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Abstract

In basic media O‐Benzoyl‐ and O‐acetyl‐2‐benzylaminobenzamide oxime (8b, c) give 5‐substituted 3‐(2‐benzylaminophenyl)‐1,2,4‐oxadiazoles (9a, b), while on heating in pure water 2‐amino‐1‐benzylbenzimidazole (10) is formed. Reaction of 2‐(N‐acylbenzylamino)benzonitrile (12) with hydroxylamine, or treatment of O‐acyl‐2‐(N‐benzoylbenzylamino)benzamide oximes (8f, g) with acid give the novel 1,2‐disubstituted 4(1H)‐quinazolone oximes 13, which isomerize on heating with alkali by an ANRORC mechanism to the 1,2,4‐oxadiazoles 9a, b.

Original languageEnglish
Pages (from-to)1107-1112
Number of pages6
JournalChemische Berichte
Volume122
Issue number6
DOIs
Publication statusPublished - Jan 1 1989

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Keywords

  • 1,2,4‐Oxadiazoles
  • 4(1H)‐Quinazolone oximes
  • ANRORC mechanism

ASJC Scopus subject areas

  • Chemistry(all)

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